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  • Mark Losh

How to Build a Winning Sales Playbook - A sports analogy

I'm a lifelong sports fan. An aging, X-competitive Athlete, X-high school Varsity Football and Baseball Coach, and X-Basketball Official. Tons of "Xs", now for some "Os." Oh, and I love sports analogies - particularly when it comes to the Leadership, Sales and Entrepreneurial psyche! From my playing and coaching experiences, Football is the team sport which has the most comprehensive of all Playbooks. Thus, hopefully, suits my illustration well. And let's face it, Enterprise Software sales IS a contact sport.

In my first VP of Sales role, I was a control freak. i was 30 and wanted to manage rep's activities, methods, and behaviors. I knew best. I tried to develop THE end-all sales methodology and define it's steps in ACT! - it was 1992. The tool was cumbersome, the process was mine (not the team's), few used it, and the project was a disaster.

Fast forward to today. SaaS has blurred the lines between Marketing, Sales, Services, and Support. Prospects and Tech Buyers are far more savvy. Forrester notes,

"In a recent survey, 74% of business buyers told us they conduct more than half of their research online before making an offline purchase. This buyer dynamic changes the role of B2B marketing in a fundamental way."

Gartner, Forrester and other research firms are assisting Corporate Buyers develop their own Buyer Journey Maps.

Enterprise Software Organizations need to adequately prepare before engaging a prospect to improve win / loss ratios, reduce CAC (Customer Acquisition Costs), increase LTV (Lifetime Value of a Customer), and reduce the all important churn rate of the SaaS sales and delivery model.



1) WHY develop one?

-THE CHANGING TECH BUYER- According to Forrester:

  • 70% of B2B technology spending is business-led or heavily influenced by business leaders

  • 85% of tech buyers expect to consume at least 3 pieces of content prior to contacting sales

  • 50% of business leaders believe that technology is too important for them not to be involved in the decision

2) WHO should be involved in the creation?

All organizational teams involved in interfacing with Customers and Partners should be involved in the development of a Sales Playbook (Marketing, Sales, Business Development, Services, and Support). Clearly, Marketing should take ownership for the creation of consistent branded messaging which meets the needs of both Sales and the Customer. In my experience, team participation and buy-in is paramount!

3) WHAT content should be included?

Each Organization will be different, but the basics should include:

  • The Buyers Journey Map (What are the Buyer's expectations? RFP, Trial, POC, competitive, etc)

  • Market Analysis - Segmentation, patterns, and trends

  • Opportunity Qualification Tools - Need, budget, buyer, influencer, roadblocks

  • Target Account Profiles - Defines opportunity for which we should win 100% of deals

  • Messaging in various forms - Value Proposition, Unique Differentiators, Competitive Analysis

  • Conversation Points - Try to avoid scripts. Top Athletes are adept at "Open Field Running"

  • Sales Process - Definitive steps act as First Down Markers to move the chains

  • Forecasting Tools - Be Accountable! Definitions, requirements

  • Performance Metrics - How is the team, team member being evaluated? Shared KPIs, etc.

  • Roles and Responsilbilities - Each team member needs to know his/her assignment

  • Partner Ecocystem - When to use, role played, Influencers

  • Presentations - Corporate, Vertical, Use Case - PowerPoint, Webinars, etc.

  • Demonstrations - Online, canned vs. custom

  • White Papers - Use Cases, Success Stories, etc.

  • POC (Proof of Concept) Guidelines - Rules of Engagement, Success Criteria, Agreement

  • Pricing Models and Quote Tools - Automated tools

  • ROI calculators - Customizable for each Prospect scenario

  • Licensing Agreements - Product, Service, Support, NDA, Partner - be equipped!

4) WHEN is the Playbook used?

Studied intently during onboarding, reviewed frequently, and updated often.

As Coaches, we'd prepare intensively in the off-season attending seminars and camps learning the "best practices" of colleagues in the profession. We'd feverishly update our Playbooks and philosophies prior to Training Camp (Training and Onboarding). During Training Camp, we'd repetitively practice our core offensive set of plays. As the season began, we'd prepare for each week's game by focusing on a set of plays which we believed would work best against that particular opponent (Qualified Opportunity). Yet, we'd be prepared to adjust our game plan and play calling as the game situation and defenses (Competitors) presented themselves. Following a game, we'd dive into film reviews, grading each players execution against his assignment. We'd grade the overall team, and ourselves as a Staff (360 degree reviews). Did the players execute? Did we call the right plays, defenses? Did we prepare and motivate the players properly? Do we need to pass more frequently, or mix up our tendencies?

Monday Sales Team meetings are a great opportunity to review, reflect on wins / losses, and of course strategize on current opportunities. Staff meetings and brown bag lunches are also good opportunities to discuss strategy and share learned insights. All involved should take these insights and update the Sales Playbook. Make this a continual process - not an annual review.

5) WHERE & HOW should the Playbook be implemented and maintained?

Marketing, Sales Force, Service and Support Automation tools have become increasing integrated and much easier to use. Sales Enablement tools used in conjunction with a CRM tool can deliver compelling measurable results. Selection of various technologies is beyond the scope of this article, but most experts agree it's crucial to get a handle on the Sales Process prior to applying automation.




Winning football teams typically lead in "time of possession", and thus control the flow of the game. The same is true of successful Enterprise Sales organizations. Control the Market Message and tempo of the Sales Process and you'll likely increase the Number of Opportunities (#), Deal Value ($), Win Rate (%), and reduce the Length of the Sales Cycle (L), thus increasing your Sales Velocity (V).


ALSO, BIGGER SALES "Companies with best-in-class sales enablement strategies experience 13.7% annual increase in deal size or contract value." –Aberdeen, 2015

MORE GROWTH "Aligning sales and marketing is proven to deliver 19% more growth." –Sirius Decisions, 2015

MORE LEADS "Marketing teams with high visibility into content utilization see 33% more leads accepted by Sales." –Aberdeen, 2015

MORE QUOTAS NAILED "84% of reps achieve quota at companies with best-in-class sales .. strategies." –Aberdeen, 2015

MORE REVENUE "Businesses whose sales and marketing teams are aligned achieve 208% higher marketing revenue when compared to misaligned teams." – Hubspot, 2015


Bill Walsh was the architect of the West Coast offense. Walsh stated, "My philosophy has been to control the ball with the forward pass. To do that we have to have versatility-versatility in the action and types of passes thrown by the quarterback." Peyton Manning changed the flow of games by skipping huddles and calling audibles at the line of scrimmage.

A well developed Sales Playbook allows Sales Team Leads (Account Managers, District Sales Managers, etc) to control the flow and cadence of the Sales Engagement - calling audibles, changing plays, and bringing in the appropriate resources as required.

Another significant benefit I often witness is improved Organizational alignment and better communication between Marketing, Sales, Business Development, and Services.


I'm fond of Team Sports and the similarities to winning Sales Teams

Good luck to all! Please share your thoughts and experiences.

If your team is in need of a Sales Play Book tuneup, contact me.

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